Sodium Bicarbonate → HCID 67236011, compound

HRID 447163Notes

Reaction equation

HRID 447163 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([C:23](OCC)=[O:24])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].C(=O)(O)[O-].[Na+]>C1COCC1>[OH:24][CH2:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[S:15][C:16]=2[CH:22]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 67236140HCID 67236140, compound

Product 1

HCID 67236011HCID 67236011, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylate (1.1 g) was dissolved in dry THF (50 mL) and lithium borohydride (67 mg) was added. The resulting mixture was stirred overnight at room temperature, then heated to reflux for 24 hours. Saturated aqueous sodium bicarbonate was added and the resulting mixture was extracted with ethyl acetate. The resulting solution was concentrated to yield tert-butyl 4-(6-(hydroxymethyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate as a white solid (1.0 g). MS: 350.3 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-6631130a907c4973a12d54452a0e314d
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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