HCID 67353085, compound → tert-Butyl [(1R,3S)-3-aminocyclopentyl]carbamate

HRID 1257634Notes

Reaction equation

HRID 1257634 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:12][CH2:11][C@H:10]([NH:13]C(OCC=C)=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.CO>[NH3:7].[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 67353085HCID 67353085, compound

Product 2

HCID 222AmmoniaYield 0%HCID 45091934tert-Butyl [(1R,3S)-3-aminocyclopentyl]carbamateYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Following the procedure for ((1R,3R)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester the title compound was prepared from ((1R,3S)-3-allyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester with further purification by column chromatography on silica gel (gradient: 0 to 5% methanol in DCM then 0 to 10% 2M NH3 in methanol solution in DCM) to afford 300 mg (56%) of ((1R,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester. LCMS (Method I, ESI): RT=0.32 min, m+H-Boc=101.2; 1H NMR (400 MHz, DMSO) δ: 6.84 (s, 1H), 3.77-3.69 (m, 1H), 3.21 (m, 2H), 2.00 (m, 1H), 1.78-1.63 (m, 2H), 1.50 (m, 1H), 1.37 (s, 9H), 1.17 (m, 1H).

Sources & evidence

ORD record
ord-2c80160adc8b4582bb48d055449e6883
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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