(Cyano-phenyl-methyl)-carbamic acid tert-butyl ester → HCID 15284550, compound

HRID 964040Notes

Reaction equation

HRID 964040 reaction equation
[NH2:1][CH:2]1[CH2:6][N:5]([C@@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])[CH2:4][C:3]1([CH3:16])[CH3:15].[C:17]([O:21][C:22](NC(C1C=CC=CC=1)C#N)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[C:17]([O:21][C:22]([NH:1][CH:2]1[CH2:6][N:5]([C@@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])[CH2:4][C:3]1([CH3:15])[CH3:16])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 4231037(Cyano-phenyl-methyl)-carbamic acid tert-butyl esterHCID 15284549HCID 15284549, compound

Product 1

HCID 15284550HCID 15284550, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 3.69 g of 4-amino-3,3-dimethyl-1-[1-(R)-phenylethyl]-pyrrolidine in 40 ml of anhydrous tetrahydrofuran there was added 4.92 g of 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile and the mixture was stirred at room temperature for 1 hr. Solvent was removed under reduced pressure, and to the residue there was added ethyl acetate. The mixture was washed with a 1N sodium hydroxide aqueous solution three times and then dried. Solvent wa then removed under reduced pressure. The residue was purified through column chromatography using 200 g of silica gel in a column with chloroform as the eluant containing from 1% to 5% methanol to yield 4.32 g of the titled compound. 1H-NMR(CDCl3) δ ppm;1.00, 16(each 3H, s), 1.40(3H, d, J=7.2 Hz), 1.52(9H, s), 2.00-3.62(5H, m), 3.85-4.10(1H, m), 4.90(1H, bs), 7.38(5H, s)

Workup

  1. customSolvent was removed under reduced pressure
  2. additionto the residue there was added ethyl acetate
  3. washThe mixture was washed with a 1N sodium hydroxide aqueous solution three times
  4. customdried
  5. customSolvent wa then removed under reduced pressure
  6. customThe residue was purified through column chromatography
  7. additioncontaining from 1% to 5% methanol

Sources & evidence

ORD record
ord-5534424320a84165b36668a2812432e5
Source dataset
uspto-grants-1998_06
Patent number
US05767127

Reaction notes

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