Borane,N-dimethylmethanamine (1:1) → 4-tert-Butyl-2-(1-Boc-piperidin-4-yloxy)benzyl Alcohol

HRID 644204Notes

Reaction equation

HRID 644204 reaction equation
[B-][N+](C)(C)C.[C:6]([C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[C:12]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>O1CCCC1>[C:6]([C:10]1[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[C:12]([O:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)[CH:11]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 6327651Borane,N-dimethylmethanamine (1:1)2×HCID 685305052-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid

Product 1

HCID 576024554-tert-Butyl-2-(1-Boc-piperidin-4-yloxy)benzyl Alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of borane-trimethylamine complex (1.35 mL of a 1 M solution in tetrahydrofuran) in tetrahydrofuran (3 mL) stirring at 0° C., a solution of 4-(tert-butyl)-2-(1-Boc-piperidine-4-yloxy)benzoic acid (0.51 g, 1.35 mmol) in tetrahydrofuran (7 mL) was added slowly via cannula. After the addition was complete the reaction mixture was stirred at room temperature for 4 h, then an additional amount of borane-trimethylamine complex was added (1.35 mL of a 1 M solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for another 2 h. After quenching with ice, the mixture was partitioned between brine and dichloromethane. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to a residue (0.42 g, 86%) which was identified as the title compound and used directly in the next step without further purification.

Workup

  1. additionAfter the addition
  2. stirringThe reaction mixture was stirred at room temperature for another 2 h
  3. customAfter quenching with ice
  4. customthe mixture was partitioned between brine and dichloromethane
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (3×)
  7. dry with materialThe combined organic layers were dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a residue (0.42 g, 86%) which
  10. customused directly in the next step without further purification

Sources & evidence

ORD record
ord-5ad024ed9eab4731b63f80926786e823
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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