tert-butyl N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate

• ChemBase ID: 150435
• Molecular Formular: C14H21NO3
• Molecular Mass: 251.32144
• Monoisotopic Mass: 251.15214354
• SMILES: CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)CO
• Canonical SMILES: OC[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C14H21NO3/c1-14(2,3)18-13(17)15-12(10-16)9-11-7-5-4-6-8-11/h4-8,12,16H,9-10H2,1-3H3,(H,15,17)/t12-/m1/s1
• InChIKey: LDKDMDVMMCXTMO-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• Synonyms: N-[(1R)-1-(Hydroxymethyl)-2-phenylethyl]carbamic Acid 1,1-Dimethylethyl Ester; (2R)-N-tert-Butoxycarbonyl-1-hydroxy-3-phenyl-2-propanamine; (R)-(-)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol; tert-Butyl [(1R)-1-Benzyl-2-hydroxyethyl]carbamate; N-Boc-D-phenylalaninol; (R)-tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate; (R)-(+)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol; (R)-2-(Boc-amino)-3-phenyl-1-propanol; N-(tert-Butoxycarbonyl)-D-phenylalaninol; Boc-D-phenylalaninol; (R)-(+)-2-(叔丁氧羰基氨基)-3-苯基-1-丙醇; (R)-2-(Boc-氨基)-3-苯基-1-丙醇; N-(叔丁氧基羰基)-D-苯丙氨醇; N-Boc-D-苯丙氨醇

Database IDs

• CAS Number: 106454-69-7
• MDL Number: MFCD00216472
• Beilstein Number: 4686134
• PubChem SID: 24871633; 162244596
• PubChem CID: 7019371

CALCULATED PROPERTIES

• Acid pKa: 14.370082
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.2494378
• LogD (pH = 7.4): 2.2494378
• Log P: 2.2494378
• Molar Refractivity: 70.1219 cm^3
• Polarizability: 27.580263 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 95-98 °C; 95-98 °C(lit.)
• Optical Rotation: [α]20/D +27±2°, c = 1% in methanol; [α]23/D +24°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, TLC); 98%
• Grade: puriss.
• Linear Formula: C6H5CH2CH[NHCO2C(CH3)3]CH2OH

DETAILS

Sigma Aldrich - 479594

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 15486

Other Notes
Chiral building block; the aldehyde obtained upon oxidation is used for many transformations1,2,3

Toronto Research Chemicals - B661570

Protected D-Phenylalaninol, an intermediate in the preparation of (S)-Amphetamine.

REFERENCES

• Flentge, C., et al.: Bioorg. Med. Chem. Lett., 19, 5444 (2009)
• Ji, H., et al.: J. Med. Chem., 52, 779 (2009)