Hydrochloric Acid → rac-tert-butyl N-[(1R,2R)-2-aminocyclopropyl]carbamate hydrochloride

HRID 1504817Notes

Reaction equation

HRID 1504817 reaction equation
[ClH:1].[C@@H:2]1([NH:13]C(=O)OC(C)(C)C)[CH2:4][C@H:3]1[NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>C(OCC)(=O)C>[ClH:1].[NH2:13][C@@H:2]1[CH2:4][C@H:3]1[NH:5][C:6](=[O:12])[O:7][C:8]([CH3:10])([CH3:9])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90354416di-tert-butyl rel-(1R,2R)-cyclopropane-1,2-diylbiscarbamate

Product 1

HCID 57364724rac-tert-butyl N-[(1R,2R)-2-aminocyclopropyl]carbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

37% hydrochloric acid (40.0 mL) in ethyl acetate (300 mL) was added dropwise to a solution of di-tert-butyl rel-(1R,2R)-cyclopropane-1,2-diylbiscarbamate (80.0 g) in ethyl acetate (500 mL) at 0° C. The reaction mixture was warmed to ambient temperature. After 16 hours, the reaction mixture was filtered. The collected solids were washed with diethyl ether and then dried under reduced pressure to afford tert-butyl rel-[(1R,2R)-2-aminocyclopropyl]carbamate HCl salt. MS ESI calc'd. for C8H17N2O2 [M+H]+ 173. found 173. 1H NMR (300 MHz, DMSO-d6) δ: 8.36 (bs, 3H), 7.14 (s, 1H), 2.87-2.86 (m, 1H), 2.50-2.49 (m, 1H), 1.39 (s, 9), 1.09-1.02 (m, 1H), 0.92-0.86 (m, 1H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe collected solids were washed with diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-2e7463e2fe254e6a9732b48928eef774
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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