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

HRID 1241355Notes

Reaction equation

HRID 1241355 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,cis)-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-bfec8350f8d64ec494103f79317c6cde
Source dataset
uspto-grants-2006_10
Patent number
US07115590B1

Reaction notes

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