L-Threonine → 3-Amino-1-(3-bromophenyl)propan-1-ol

HRID 1967716Notes

Reaction equation

HRID 1967716 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.C[C@@H](O)[C@H](N)C(O)=O>>[NH2:11][CH2:10][CH2:9][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[OH:12]

Participants

3

Reactant 2

HCID 6288L-ThreonineHCID 576083633-(3-Bromophenyl)-3-hydroxypropanenitrile

Product 1

HCID 576083343-Amino-1-(3-bromophenyl)propan-1-ol

Procedure

Reduction of 3-(3-bromophenyl)-3-hydroxypropanenitrile following thre method used in Example 50 gave 3-amino-1-(3-bromophenyl)propan-1-ol as a light green oil. Yield (2.30 g, 84%.) This material was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.49 (m, 1H), 7.37 (dt, J=7.2, 1.6 Hz, 1H), 7.23-7.31 (m, 2H), 4.66 (t, J=6.8 Hz, 1H), 2.61 (m, 2H), 1.61 (q, J=6.8 Hz, 2H).

Sources & evidence

ORD record
ord-13991a7c3dd74a7bbe969e22b32f6b6e
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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