Water → HCID 67324433, compound

HRID 1401793Notes

Reaction equation

HRID 1401793 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]3[CH:31]=[CH:30][C:29]4[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=4[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.O.CC(=O)OCC>C1COCC1>[CH3:32][C:28]1([CH3:33])[CH2:27][CH2:26][C:25]([CH3:34])([CH3:35])[C:24]2[CH:23]=[C:22]([C:20]3[N:21]=[C:17]([N:14]4[CH2:15][CH2:16][CH:11]([NH:10][CH2:9][CH:7]5[CH2:8][CH:6]5[CH2:4][OH:3])[CH2:12][CH2:13]4)[S:18][CH:19]=3)[CH:31]=[CH:30][C:29]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 67324371HCID 67324371, compound

Product 1

HCID 67324433HCID 67324433, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

49 mg (0.10 mmol) of 2-({1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}methyl)cyclopropanecarboxylic acid ethyl ester from step a were dissolved in 2 ml of THF under nitrogen. 475 μl of a 1M diisobutylaluminium hydride solution in THF were added dropwise. The mixture was stirred at 60° C. overnight, water and EA were added, the mixture was filtered through Cellite, evaporated and purified by means of flash chromatography on silica gel.

Workup

  1. filtrationthe mixture was filtered through Cellite
  2. customevaporated
  3. custompurified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-ed98d2f6d7304d5888457165d1f25796
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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