Methanol → HCID 22493824, compound

HRID 457350Notes

Reaction equation

HRID 457350 reaction equation
[BH4-].[Na+].O1C2C=CC(CN(CC3C=CC4OCOC=4C=3)[CH2:14][C:15]3[N:16]([CH2:27][CH2:28][CH2:29][CH3:30])[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18][C:19]=3Br)=CC=2OC1.C[OH:42]>>[CH2:27]([N:16]1[C:15]([CH2:14][OH:42])=[CH:19][N:18]=[C:17]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 18437480HCID 18437480, compound

Product 1

HCID 22493824HCID 22493824, compound

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (1.135 g, 30 mmol) is added to a solution of aldehyde 138 (6.849 g, 30 mmol) in 100 ml of methanol cooled to 0° C. The resulting solution is stirred at 0° C. for 30 min, evaporated and the residue dissolved in 150 ml of ethyl acetate, washed with water and brine, dried over Na2SO4, concentrated and taken to dryness under high vacuum to give the product 139 as an oil. MS (+VE) m/z 231 (M+1).

Workup

  1. customevaporated
  2. dissolutionthe residue dissolved in 150 ml of ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-99b8e2062de340aeac468cf3038a48a3
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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