Methylamine → HCID 118390049, compound

HRID 1477947Notes

Reaction equation

HRID 1477947 reaction equation
CN.O=[C:4]1[C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5]1.[BH3-][C:21]#[N:22].[Na+]>>[CH3:21][NH:22][CH:4]1[C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5]1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 1183900101810076-94-8

Product 1

HCID 118390049HCID 118390049, compoundYield 100%

Procedure

To a solution of CH3NH2 (33% [w/w] in EtOH, 11.70 g, 124.3 mmol) was added tert-butyl 4-oxo-2-azaspiro[4.4]nonane-2-carboxylate (5.92 g, 24.7 mmol). After addition, the reaction mixture was stirred at rt overnight, and then NaBH3CN (4.69 g, 74.6 mmol) was added portionwise. The resulting mixture was stirred at rt for 2 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc, 100%) to give the product as colorless oil (6.28 g, 100%).

Workup

  1. additionAfter addition
  2. stirringThe resulting mixture was stirred at rt for 2 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (EtOAc, 100%)

Sources & evidence

ORD record
ord-28bef9c3e2ec4a9faa7a5bb5321ddd49
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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