Sodium cyanoborohydride → tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamate

HRID 1907270Notes

Reaction equation

HRID 1907270 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[BH3-]C#[N:31].[Na+]>CO>[NH2:31][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:20][CH2:19][CH2:18][N:10]([C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:9])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 59190380(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate

Product 1

HCID 67043294tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (193 mg, 0.43 mmol) and NH4OAc (670 mg, 8.6 mmol) in MeOH (15 mL) was added NaCNBH3 (270 mg, 4.3 mmol). The mixture was heated at reflux for 22 h and concentrated under reduced pressure. The residue was partitioned between 1 M aq NaOH (25 mL) and CH2Cl2 (2×50 mL). The combined CH2Cl2 layers were washed with brine (15 mL), dried over Na2SO4 and concentrated to afford tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamate (179 mg, 93%) as an oil which was used without further purification. LC-MS Method 1 tR=1.57 min, m/z=449, 447.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 22 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 1 M aq NaOH (25 mL) and CH2Cl2 (2×50 mL)
  5. washThe combined CH2Cl2 layers were washed with brine (15 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-620f53a0f18d4a19a5e25b1a76ebc37a
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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