Sodium borohydride → HCID 58119742, compound

HRID 2368642Notes

Reaction equation

HRID 2368642 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([O:23][CH3:24])[CH3:22])[C:12]([C:25](=[O:36])[C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[C:11]([CH:37]3[CH2:42][CH2:41][N:40]([C:43]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[O:44])[CH2:39][CH2:38]3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([O:23][CH3:24])[CH3:22])[C:12]([CH:25]([OH:36])[C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=3)=[C:11]([CH:37]3[CH2:42][CH2:41][N:40]([C:43]([O:45][CH2:46][C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)=[O:44])[CH2:39][CH2:38]3)[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58119718HCID 58119718, compound

Product 1

HCID 58119742HCID 58119742, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

959 mg (6) Benzyl 4-((5S)-5-(tert-butyldimethylsilyloxy)-2-(1-methoxyethyl)-7,7-dimethyl-3-(4-(trifluoromethyl)benzoyl)-5,6,7,8-tetrahydroquinolin-4-yl)piperidine-1-carboxylate (Example VI (69) are dissolved in 15 ml ethanol. To the mixture 441 mg of sodiumborohydride is added. The reaction is stirred for 2 hours at 70° C. Then 8 equivalents of sodiumborohydride are added and the reaction is stirred over night at 70° C. The solvent is evaporated under vacuum. Water, ethylacetate and 1M hydrochloric acid are added. The aqueous phase is extracted with ethylacetate and the combined organic phases are washed with brine. After drying with natrium sulphate the solvents are evaporated under vacuum and the residue is chromatographed on isolate.

Workup

  1. stirringthe reaction is stirred over night at 70° C
  2. customThe solvent is evaporated under vacuum
  3. additionWater, ethylacetate and 1M hydrochloric acid are added
  4. extractionThe aqueous phase is extracted with ethylacetate
  5. washthe combined organic phases are washed with brine
  6. dry with materialAfter drying with natrium sulphate the solvents
  7. customare evaporated under vacuum
  8. customthe residue is chromatographed
  9. customon isolate

Sources & evidence

ORD record
ord-0cbdeebce609487db45703cbde4c6979
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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