Trifluoroacetic acid methylene chloride → (3S,7S)-3-amino-1-methyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one

HRID 1392070Notes

Reaction equation

HRID 1392070 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:14][CH:13]=[CH:12][C@@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]([CH3:21])[C:9]1=[O:22])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>C(Cl)Cl.C([O-])(O)=O.[Na+]>[NH2:7][C@H:8]1[CH2:14][CH:13]=[CH:12][C@@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]([CH3:21])[C:9]1=[O:22]

Participants

5

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 58691177tert-butyl[(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

Product 1

HCID 10242432(3S,7S)-3-amino-1-methyl-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-oneYield 93.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To the tert-butyl[(3S,7S)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (1d) (200 mg) was added a 1:3 mixture of TFA/DCM (2 ml). The reaction mixture was stirred for 1 h, then diluted with DCM and saturated aq. NaHCO3. The organic layer was isolated and washed with saturated aq. NaHCO3, brine, dried (Na2SO4) and concentrated to yield an oil (128 mg, 93%). MS APCI, m/z=217 (M+1). LC/MS 1.55 min., Method A.

Workup

  1. customThe organic layer was isolated
  2. washwashed with saturated aq. NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-851c11cc1eb74697a3797978b990c0b5
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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