Water → 2-[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-ethanol

HRID 1876312Notes

Reaction equation

HRID 1876312 reaction equation
C[O:2][C:3](=O)[CH2:4][C@@H:5]1[CH2:9][S:8][C:7]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[NH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[N:6]1.O1CCCC1.[BH4-].[Li+].O>O1CCCC1>[Cl:19][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([NH:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:14]=1)[NH:11][C:10]([C:7]1[S:8][CH2:9][C@@H:5]([CH2:4][CH2:3][OH:2])[N:6]=1)=[CH:18]2

Participants

5

Reactant 3

HCID 962WaterHCID 25196144[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid methyl esterHCID 131718764lithium borohydride THF

Product 1

HCID 251961462-[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-ethanolYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (550 mg, 1.4 mmol) prepared in Example 26 was dissolved in tetrahydrofuran (50 ml). 1 M lithium borohydride tetrahydrofuran solution (2.11 ml, 2.11 mmol) was added thereto, and the mixture was stirred for 1 h while raising the reaction temperature from −60° C. to 0° C. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and separated by column chromatography to give the title compound (510 mg, Yield 100%).

Workup

  1. temperaturewhile raising the reaction temperature from −60° C. to 0° C
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customseparated by column chromatography

Sources & evidence

ORD record
ord-317d5deb2dfa4603a880361197727009
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

Loading…