Benzonitrile, 3-(bromomethyl)- → (2R,3R)-1-t-Butyloxycarbonyl-3-((3-cyanophenyl)methyloxy)-2-phenylpiperidine

HRID 1439939Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[C@H:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-

HCID 215840931-t-Butyloxycarbonyl-3-hydroxy-2-phenylpiperidine

Product 1

HCID 53964633(2R*,3R*)-1-t-Butyloxycarbonyl-3-((3-cyanophenyl)methyloxy)-2-phenylpiperidine

Procedure

This compound was prepared from 1-t-butyloxycarbonyl-3-hydroxy-2-phenylpiperidine (Description 1c) and α-bromo-m-tolunitrile according to the procedure described in Example 1d. 1H NMR (360 MHz, CDCl3) δ 1.49 (9H, s, (CH3)3), 1.6-1.72 (2H, m), 1.87-1.99 (2H, m), 2.72 (1H, dt, J=13, 4 Hz, NCHH), 3.80-3.95 (2H, m, CHO+NCHH), 4.65 (2H, q, J=12 Hz, OCH2), 5.69 (1H, brs, CHPh), 7.1-7.5 (9H, m, ArH).

Sources & evidence

ORD record: ord-6b2afaae6b7c471badbcf6832960ac03
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496833

Reaction notes

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