Sodium borohydride → [5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazol-2-yl]-methanol

HRID 644058Notes

Reaction equation

HRID 644058 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:10]2[C:18]3[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:11]=2)=[CH:8][N:9]=1)=O.[BH4-].[Na+]>CO.O1CCCC1>[CH:22]1([CH2:21][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[C:10]([C:7]3[S:6][C:5]([CH2:3][OH:2])=[N:9][CH:8]=3)=[CH:11]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 687007055-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazole-2-carboxylic acid methyl ester

Product 1

HCID 68697636[5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazol-2-yl]-methanolYield 78.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazole-2-carboxylic acid methyl ester (418 mg, 1.09 mmol) in methanol (10 ml) and tetrahydrofuran (10 ml) was added sodium borohydride (83 mg, 2.18 mmol) portionwise over 2 minutes. The reaction was stirred for a further 1 h and then quenched with aqueous hydrochloric acid (1M; 10 ml). The mixture was poured into a separating funnel, diluted with dichloromethane (50 ml) and washed with water (20 ml). The combined organic layers were dried, filtered and the solvent removed in vacuo to leave a yellow oil. The oil was purified by flash column chromatography using 50-100% (v/v) diethyl ether in heptane to give [5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazol-2-yl]-methanol (308 mg, 0.86 mmol) as an off-white foam.

Workup

  1. customquenched with aqueous hydrochloric acid (1M; 10 ml)
  2. additionThe mixture was poured into a separating funnel
  3. additiondiluted with dichloromethane (50 ml)
  4. washwashed with water (20 ml)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto leave a yellow oil
  9. customThe oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-55f5fcb0f20b43feb753f8e51f503232
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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