Water → [4-(4-Benzyl-morpholin-2-yl)-phenyl]-methanol

HRID 2167860Notes

Reaction equation

HRID 2167860 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:20][CH:21]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 866700124-(4-Benzyl-morpholin-2-yl)-benzaldehyde

Product 1

HCID 67032692[4-(4-Benzyl-morpholin-2-yl)-phenyl]-methanolYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-benzyl-morpholin-2-yl)-benzaldehyde (1.19 g; 4.23 mmol) in MeOH (25 mL) was added NaBH4 (0.16 g; 4.23 mmol), in small portions, at 0° C. After the addition was complete the mixture was allowed to warm to RT and stirred for one hour. Subsequently, the mixture was cooled to 0° C., water was added, and the MeOH evaporated in vacuo. To the aqueous solution was added a 5% aqueous NaHCO3 solution and EtOAc. The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford [4-(4-benzyl-morpholin-2-yl)-phenyl]-methanol (1.16 g) which was used as such.

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. temperatureSubsequently, the mixture was cooled to 0° C.
  4. customthe MeOH evaporated in vacuo
  5. additionTo the aqueous solution was added a 5% aqueous NaHCO3 solution and EtOAc
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15187b2cc7174fb2a4a98bb46d9599e6
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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