Methylamine → 7-Azaspiro[4.5]decane-7-carboxylic acid, 2-(methylamino)-, 1,1-dimethylethyl ester

HRID 1478003Notes

Reaction equation

HRID 1478003 reaction equation
CN.O=[C:4]1[CH2:8][CH2:7][C:6]2([CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)[CH2:5]1.[BH3-][C:22]#[N:23].[Na+]>>[CH3:22][NH:23][CH:4]1[CH2:8][CH2:7][C:6]2([CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)[CH2:5]1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 118173849tert-butyl 2-oxo-7-azaspiro[4.5]decane-7-carboxylate

Product 1

HCID 1181738087-Azaspiro[4.5]decane-7-carboxylic acid, 2-(methylamino)-, 1,1-dimethylethyl esterYield 100%

Procedure

To a solution of CH3NH2 (33% [w/w] in EtOH, 2 mL) was added tert-butyl 2-oxo-7-azaspiro[4.5]decane-7-carboxylate (197 mg, 0.78 mmol) and the reaction mixture was stirred at rt overnight. Then NaBH3CN (74 mg, 1.17 mmol) was added and the resulting mixture was stirred at rt for another 2 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/20) to give the title compound as colorless oil (208 mg, 100%).

Workup

  1. stirringthe resulting mixture was stirred at rt for another 2 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/20)

Sources & evidence

ORD record
ord-dc5ee5f98a2849c9a1dbd192a48c228c
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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