Diisobutylaluminum hydride → HCID 72725459, compound

HRID 591350Notes

Reaction equation

HRID 591350 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([CH2:25][C:26](OCC)=[O:27])[N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.C(O)(=O)C(C(C(O)=O)O)O.[Na]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([CH2:25][CH2:26][OH:27])[N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 45051801HCID 45051801, compoundHCID 89612750HCID 89612750, compound

Product 1

HCID 72725459HCID 72725459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of ethyl 2-(2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)thiazol-4-yl)acetate (86.4 mg, 0.2 mmol, 1 equiv) in dried CH2Cl2 (3 mL) under N2 at room temperature was then slowly added DIBAL-H (1M in CH2Cl2, 1 mL, 1 mmol, 5 equiv). The resulting mixture became a clear solution and was stirred at room temperature for 1 h. The resulting mixture was slowly poured into a vigorously stirred mixture of CH2Cl2/10 wt % sodium tartaric acid (aq) (10 mL/10 mL). The resulting mixture was stirred for 1 h and the layers were separated. The aqueous layer was extracted with CH2Cl2 (30 mL×2). The combined organic layer was dried (Na2SO4) and filtered. The solvent was removed by roto-evaporator and the resulting residue purified by column using 80-90% EtOAc/hexane as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(4-(2-hydroxyethyl)thiazol-2-yl)piperidine-1-carboxamide.

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (30 mL×2)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customThe solvent was removed by roto-evaporator
  7. customthe resulting residue purified by column

Sources & evidence

ORD record
ord-d3857afdff3a4592902776fb4345cef9
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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