Triethylamine → HCID 11237168, compound

HRID 2366989Notes

Reaction equation

HRID 2366989 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7](=[O:22])[CH2:8][NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH2:3]1.[OH:23][C:24]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(CC)CC)C>C1COCC1>[OH:23][C:24]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:25][CH2:26][CH:27]([NH:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7](=[O:22])[CH2:8][NH:9][C:10](=[O:21])[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=3)[CH2:3]2)[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5837414-Hydroxy-4-phenylcyclohexan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 57803383HCID 57803383, compound

Product 1

HCID 11237168HCID 11237168, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the pyrrolidine intermediate from step C (0.3 g, 0.85 mmol) and the ketone from step E (0.16 g, 0.85 mmol) in THF (5 mL) was added Na(OAc)3BH (0.35 g, 2.5 mmol) followed by triethylamine (0.2 mL, 1.5 mmol). The reaction was continued at room temperature overnight and quenched by addition of a saturated NaHCO3 solution. The resulting solution was extracted with EtOAc and the EtOAc layer was dried over MgSO4 and concentrated. Separation on silica gel eluting with 10% to 30% MeOH/EtOAc provided the cis (fast moving spot) and trans (slow moving spot) isomers of the title compound. MS (M+H)+ 490.0.

Workup

  1. customquenched by addition of a saturated NaHCO3 solution
  2. extractionThe resulting solution was extracted with EtOAc
  3. dry with materialthe EtOAc layer was dried over MgSO4
  4. concentrationconcentrated
  5. customSeparation on silica gel eluting with 10% to 30% MeOH/EtOAc
  6. customprovided the cis (

Sources & evidence

ORD record
ord-e60a3c365a4444af83c56266f23f06e4
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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