Methylamine → (S)-tert-butyl 1-cyclohexyl-3-(methylamino)pentan-2-ylcarbamate

HRID 451770Notes

Reaction equation

HRID 451770 reaction equation
CC1C=CC(S(O[CH:12]([CH2:29][CH3:30])[C@@H:13]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)(=O)=O)=CC=1.[CH3:31][NH2:32]>>[CH:15]1([CH2:14][C@H:13]([NH:21][C:22](=[O:23])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:12]([NH:32][CH3:31])[CH2:29][CH3:30])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 59201516(S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate

Product 1

HCID 59201714(S)-tert-butyl 1-cyclohexyl-3-(methylamino)pentan-2-ylcarbamate

Procedure

A solution of (S)-2-(tert-butoxycarbonylamino)-1-cyclohexylpentan-3-yl 4-methylbenzenesulfonate (640 mg, 1.46 mmol) in 33% MeNH2 (in EtOH) (0.02 M) was heated to 60° C. for 1 h in a pressure sealed vessel. The solvent was removed under reduced pressure to give (S)-tert-butyl 1-cyclohexyl-3-(methylamino)pentan-2-ylcarbamate. MS ESI +ve m/z 299 (M+H).

Workup

  1. customsealed vessel
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-19e29e43556442f3a868118d2258fc34
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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