Hydrochloric Acid → Tert-butyl(3s,4s)-4-{[4-(4-fluorobenzyl)cyclohexyl]amino}tetrahydro-3-furanylcarbamate

HRID 397166Notes

Reaction equation

HRID 397166 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@@H:8]1[CH2:12][O:11][CH2:10][C@H:9]1[NH2:13])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>ClCCCl>[F:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[CH2:26][CH2:25][CH:24]([NH:13][C@@H:9]3[CH2:10][O:11][CH2:12][C@H:8]3[NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:23][CH2:22]2)=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 121339524-[(4-Fluorophenyl)methyl]-cyclohexanoneHCID 69588176tert-Butyl ((3S,4S)-4-aminotetrahydrofuran-3-yl)carbamate

Product 1

HCID 69588322Tert-butyl(3s,4s)-4-{[4-(4-fluorobenzyl)cyclohexyl]amino}tetrahydro-3-furanylcarbamateYield 57%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a flame-dried round bottom flask under nitrogen containing (3S,4S)-3-aminotetrahydrofuran-4-yl carbamic acid tert-butyl ester (90 mg, 0.45 mmol) and 4-(4-fluorobenzyl)cyclohexanone (87 mg, 0.42 mmol) in 1,2-dichloroethane (6 mL) was added sodium triacetoxyborohydride (191 mg, 0.90 mmol). The resulting yellow mixture was stirred for 15 min and was then poured into 1 N aqueous hydrogen chloride (50 mL). The aqueous layer was basified with 50% aqueous sodium hydroxide and washed with ethyl acetate (4×20 mL). The combined organic layers were dried over sodium sulfate, concentrated, and the resulting residue was purified by flash chromatography (5% methanol in dichloromethane) to yield the desired carbamic acid tert-butyl ester (94 mg, 53%) as a yellow oil. MS (ESI) 393 (M+H).

Workup

  1. washwashed with ethyl acetate (4×20 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by flash chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a4a52368e6a14d33b694e552aa622582
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

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