(Cyano-phenyl-methyl)-carbamic acid tert-butyl ester → 8-tert-butoxycarbonyl-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octane

HRID 1445273Notes

Reaction equation

HRID 1445273 reaction equation
N[CH:2]1[C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:3]1.[C:18]([O:22][C:23](NC(C1C=CC=CC=1)C#N)=[O:24])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1>[C:18]([O:22][C:23]([CH:2]1[C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[CH2:3]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 4231037(Cyano-phenyl-methyl)-carbamic acid tert-butyl esterHCID 18660864HCID 18660864, compound

Product 1

HCID 685468078-tert-butoxycarbonyl-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octaneYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 2.9 g of 8-amino-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octane in 30 ml of tetrahydrofuran there was added 3.3 g of 2-(tertbutoxycarbonylamino)-2-phenylacetonitrile and the resulting mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure, and ethyl acetate was added to the resulting residue. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography using 50 g of silica gel. The column was eluted with chloroform, chloroform containing methanol and 4.1 g of the titled compound was obtained from a eluate when the eluant was chloroform containing 1% (v/v) of methanol.

Workup

  1. customThe solvent was removed under reduced pressure, and ethyl acetate
  2. additionwas added to the resulting residue
  3. washThe mixture was washed with a 1N sodium hydroxide aqueous solution three times
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting residue was purified by column chromatography
  7. washThe column was eluted with chloroform, chloroform
  8. additioncontaining methanol

Sources & evidence

ORD record
ord-7650471d1b554cbb9db4938766471ab4
Source dataset
uspto-grants-2010_02
Patent number
USRE041149E1

Reaction notes

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