HCID 66811108, compound → HCID 57911421, compound

HRID 1666130Notes

Reaction equation

HRID 1666130 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:19][CH2:18][C@H:17]([OH:20])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH2:10]1.FC1C(F)=CC=CC=1[C@H]1CC[C@@H](O)C2=NC=CC=C2C1>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1=[CH:10][C:11]2[C:12]([CH:17]([OH:20])[CH2:18][CH2:19]1)=[N:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 2

HCID 66811108HCID 66811108, compoundHCID 66811576HCID 66811576, compound

Product 1

HCID 57911421HCID 57911421, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic trans-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol and cis-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol. In a 500 mL round-bottomed flask was (E)-6-(2,3-difluorophenyl)-8,9-dihydro-7H-cyclohepta[b]pyridin-9-ol (660 mg, 2.415 mmol) in MeOH (20 mL) to give a colorless solution. Pd/C (257 mg, 0.242 mmol) was added, and the mixture was stirred under hydrogen balloon for 4 h. LCMS showed complete conversion. Filtered and concentrated to a colorless oil. Purification by FCC up to 80% EtOAc/hexane afforded two products: trans-alcohol (104.3 mg, 16%), and cis-alcohol (492.8 mg, 74%), both as white solids. Analytical data of both alcohols matched that of previously described.

Workup

  1. customIn a 500 mL round-bottomed flask was

Sources & evidence

ORD record
ord-e68136217e374b0c9c8a2c80b853dd63
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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