Sodium borohydride → 2-(2-(Tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydro-quinazolin-5-ol

HRID 1432016Notes

Reaction equation

HRID 1432016 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[N:30]=[CH:29][C:28]2[C:27](=[O:31])[CH2:26][CH2:25][CH2:24][C:23]=2[N:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Si:1]([O:18][CH2:19][CH2:20][C:21]1[N:30]=[CH:29][C:28]2[CH:27]([OH:31])[CH2:26][CH2:25][CH2:24][C:23]=2[N:22]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 588413472-(2-(tert-butyldiphenylsilyloxy)ethyl)-7,8-dihydroquinazolin-5(6H)-one

Product 1

HCID 588413372-(2-(Tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydro-quinazolin-5-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2-(tert-butyldiphenylsilyloxy)ethyl)-7,8-dihydroquinazolin-5(6H)-one (2.16 g, 5 mmol) in 30 mL of dry MeOH was treated with NaBH4 (189 mg, 5 mmol). After 5 min, the reaction was quenched with 5 mL of sat. NH4Cl solution. The MeOH was evaporated and the residue was extracted with DCM, dried over Na2SO4 and evaporated. Flash chomatography (SiO2, DCM to EtOAc) gave the desired product as a white solid.

Workup

  1. customthe reaction was quenched with 5 mL of sat. NH4Cl solution
  2. customThe MeOH was evaporated
  3. extractionthe residue was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-72733672018a48d4b43f12e4b90e340b
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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