Ammonia → HCID 68713956, compound

HRID 451654Notes

Reaction equation

HRID 451654 reaction equation
[Cl:1][C:2]1[C:3]([F:29])=[C:4]([C@H:8]([O:22][CH2:23][C:24](OCC)=[O:25])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[NH3:30]>CO>[NH2:30][C:24](=[O:25])[CH2:23][O:22][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:29])[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68710939HCID 68710939, compound

Product 1

HCID 68713956HCID 68713956, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-((R)-(3-chloro-2-fluorophenyl)(2-ethoxy-2-oxoethoxy)-methyl)piperidine-1-carboxylate (500 mg, 1.16 mmol) in MeOH (10 mL) was added NH3 (aq) (28%, 15 mL) at rt. The resulting clear solution was stirred at rt overnight. Solvent and excess ammonia was removed in vacuo to afford (R)-tert-butyl 3-((2-amino-2-oxoethoxy)(3-chloro-2-fluorophenyl)methyl)piperidine-1-carboxylate (350 mg, 0.87 mmol, 75%). 1H NMR (400 MHz, CD3OD): 1.45 (s, 9H), 1.56 (m, 1H), 1.90 (m, 1H), 2.95 (m, 2H), 3.55-3.85 (m, 3H), 4.15 (m, 1H), 4.56 (m, 1H), 7.22 (m, 1H), 7.42 (m, 2H); MS (E/Z): 401 (M+H+). The diastereomers can be separated by preparative HPLC if desired.

Workup

  1. customSolvent and excess ammonia was removed in vacuo

Sources & evidence

ORD record
ord-cfcbfee0cfc14391a68cbd4486205a01
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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