Hydrochloric Acid → ((1R,4S)-4-aminocyclopent-2-en-1-yl)methanol hydrochloride

HRID 986923Notes

Reaction equation

HRID 986923 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([NH:8]C(=O)OC(C)(C)C)[CH:5]=[CH:4]1.[ClH:16]>C(O)C>[ClH:16].[NH2:8][C@H:6]1[CH2:7][C@@H:3]([CH2:2][OH:1])[CH:4]=[CH:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18453470HCID 18453470, compound

Product 1

HCID 12899914((1R,4S)-4-aminocyclopent-2-en-1-yl)methanol hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+)-(1S,4R)-tert-Butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate (part b of this example, 10.66 g, 50.0 mmol) was refluxed in absolute ethanol (25 mL) with concentrated hydrochloric acid (5.0 mL, 60 mequiv) for 2.5 hours. Evaporation of volatiles left title compound as white solid; mass spectrum (ES): 114 (M+1); 1H-NMR (DMSO-d6) δ: 7.9 (m, 3H), 6.03 and 5.75 (two m, 2H), 4.11 (m, 1H), 3.41 (d, J=5.4 Hz, 2H), 2.8 (m, 1H), 2.36 (m, 1H), 1.4 (m, 1H). This solid was used immediately in the following example.

Workup

  1. customEvaporation of volatiles
  2. waitleft title compound as white solid

Sources & evidence

ORD record
ord-c79d5b6850c0408ba2a51ac1a8ae857e
Source dataset
uspto-grants-2003_10
Patent number
US06630477B1

Reaction notes

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