Hydrochloric Acid → HCID 69980981, compound

HRID 1637086Notes

Reaction equation

HRID 1637086 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)([OH:20])[CH2:16][CH2:15]2)[CH2:10]1)=O)(C)(C)C.[ClH:28]>C(OCC)(=O)C>[ClH:28].[ClH:28].[NH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:15][CH2:16][C:17]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)([OH:20])[CH2:18][CH2:19]2)[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54188068HCID 54188068, compound

Product 1

HCID 69980981HCID 69980981, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-((3R)-3-tert-Butoxycarbonylamino-pyrrolidin-1-yl)-1-(4-fluorophenyl) cyclohexanol (1.05 g, 2.8 mmol) in ethyl acetate (50 ml), cooled to 0° C. was added hydrogen chloride gas, bubbled in gently for 5-10 minutes. The reaction mixture was stirred for 20 minutes at 0° C. and the above procedure was repeated twice. Concentration and flushing with ethyl acetate three times gave 4-((3R)-3-aminopyrrolidin-1-yl)-1-(4-fluorophenyl) cyclohexanol dihydrochloride (0.87 g, 89%); 1H NMR (DMSO)δ 11.33 (bd, 1H)), 8.60 (bd, 3H), 7.52 (m, 2H), 7.14 (m, 2H), 5.12 (bs, 1H), 3.35-4.04 (m, 6H), 1.76-2.27 (m, 10H).

Workup

  1. custombubbled in gently for 5-10 minutes
  2. concentrationConcentration
  3. customflushing with ethyl acetate three times

Sources & evidence

ORD record
ord-6808439993204b6f9f59b16c83a8186e
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

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