Hydrochloric Acid → HCID 76849799, compound

HRID 920956Notes

Reaction equation

HRID 920956 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[C:5]([C:12](OC)=[O:13])[N:4]=1.[BH4-].[Na+].Cl>C(O)C>[F:17][C:2]([F:1])([F:16])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[C:5]([CH2:12][OH:13])[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68011843HCID 68011843, compound

Product 1

HCID 76849799HCID 76849799, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate 3b (315 mg, 1.26 mmol) was dissolved in 10 mL of ethanol, followed by addition of sodium borohydride (240 mg, 6.33 mmol). After stirring for 12 hours, the reaction mixture was added dropwise with 2 M hydrochloric acid until no gas was generated in the reaction mixture. The reaction mixture was concentrated under reduced pressure to obtain the crude [3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-1-yl]methanol 6a (230 mg) as a white solid. The product was used directly in the next reaction without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a49f8fea423e494c9a8fb9c1c3b99abf
Source dataset
uspto-grants-2016_03
Patent number
US09273052B2

Reaction notes

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