ethyl (2R)-2-amino-2-phenylpropanoate → (R)-2-Amino-2-phenylpropan-1-ol

HRID 605429Notes

Reaction equation

HRID 605429 reaction equation
[NH2:1][C@@:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:3](OCC)=[O:4].N[C@](C1C=CC=CC=1)(C)C(OCC)=O>>[NH2:1][C@@:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH2:3][OH:4]

Participants

3

Reactant 2

HCID 57186408ethyl (2R)-2-amino-2-phenylpropanoateHCID 86615568ethyl (2S)-2-amino-2-phenylpropanoate

Product 1

HCID 11040873(R)-2-Amino-2-phenylpropan-1-ol

Procedure

The title compound was prepared by the procedure of Example 445D substituting the product of Example 450B for the product of Example 445C to give a colorless viscous oil (0.57 g, 67%). [α]D23: −13.8°(c=1.05, EtOH). 1H-NMR (300 MHz, DMSO-d6) δ ppm: 1.28 (s, 3H), 1.76 (br-s, 2H), 3.39 (d, J=5.2 Hz, 2H), 4.72 (t, J=5.2 Hz, 1H), 7.12-7.20 (m, 1H), 7.22-7.32 (m, 2H), 7.44-7.54 (m, 2H). MS ESI+ m/z: 152 (M+H).

Sources & evidence

ORD record
ord-367b6e06086a4f70accc03c3f15d9ccb
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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