Methylamine → (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-(methylamino)-5-oxopentyl)piperidine-1-carboxylate

HRID 451671Notes

Reaction equation

HRID 451671 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]2([C@@H:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:28][NH2:29]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2)([OH:9])[CH2:13][CH2:12][CH2:11][C:10]([NH:29][CH3:28])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59201295(R)-tert-butyl 3-((S)-2-(3-chlorophenyl)-6-oxotetrahydro-2H-pyran-2-yl)piperidine-1-carboxylate

Product 1

HCID 59201335(R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-(methylamino)-5-oxopentyl)piperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-tert-butyl 3-((S)-2-(3-chlorophenyl)-6-oxotetrahydro-2H-pyran-2-yl)piperidine-1-carboxylate (60 mg, 0.153 mmol) was dissolved in a ca 30% solution of methylamine in methanol (3 mL). The mixture was stirred at it for 2 h then concentrated under reduced pressure to give (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-(methylamino)-5-oxopentyl)piperidine-1-carboxylate (60 mg, 93%), which was used directly without purification. 1H NMR (400 MHz, CDCl3): 1.12-1.45 (m, 3H), 1.46 (s, 9H), 1.58-1.81 (m, 6H), 2.05-2.17 (m, 2H), 2.50-2.58 (m, 2H), 2.69 (m, 3H), 4.06 (m, 1H), 4.12-4.28 (m, 2H), 7.22-7.32 (m, 3H), 7.43 (s, 1H). MS (E/Z): 425 (M+H+).

Workup

  1. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-24bdf341d7ae4ac5bf7f397ad6aa7464
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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