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

HRID 1246276Notes

Reaction equation

HRID 1246276 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 1N 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-518d64f2178046c483c56097142241e2
Source dataset
uspto-grants-2006_10
Patent number
US07126010B2

Reaction notes

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