Sodium borohydride → HCID 68700139, compound

HRID 644025Notes

Reaction equation

HRID 644025 reaction equation
C([O:3][C:4]([C:6]1[S:10][N:9]=[C:8]([C:11]2[C:19]3[C:14](=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:12]=2)[N:7]=1)=O)C.[BH4-].[Na+]>O1CCCC1.CO>[CH:23]1([CH2:22][N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[C:11]([C:8]3[N:7]=[C:6]([CH2:4][OH:3])[S:10][N:9]=3)=[CH:12]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68697255HCID 68697255, compound

Product 1

HCID 68700139HCID 68700139, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (ice/methanol bath) of 3-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester (4.0 g, 10 mmol) in tetrahydrofuran (80 ml) and methanol (80 ml) was added sodium borohydride portion-wise. The reaction was stirred for a further 20 minutes and then quenched with 1M hydrochloric acid (20 ml). The methanol and tetrahydrofuran were removed in vacuo and dichloromethane (200 ml) and 2M hydrochloric acid (50 ml) were added. The organics were separated and washed with brine (50 ml), dried over magnesium sulfate and the solvent removed in vacuo. The resulting residue was purified by flash column chromatography eluting with 50% (v/v) diethyl ether in heptane to give [3-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-[1,2,4]thiadiazol-5-yl]-methanol (3.15 g, 8.8 mmol) as a light pink solid.

Workup

  1. customquenched with 1M hydrochloric acid (20 ml)
  2. customThe methanol and tetrahydrofuran were removed in vacuo and dichloromethane (200 ml) and 2M hydrochloric acid (50 ml)
  3. additionwere added
  4. customThe organics were separated
  5. washwashed with brine (50 ml)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed in vacuo
  8. customThe resulting residue was purified by flash column chromatography
  9. washeluting with 50% (v/v) diethyl ether in heptane

Sources & evidence

ORD record
ord-ffa6f426925a4d2c8ebad46af782b595
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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