Sodium borohydride → HCID 21960097, compound

HRID 2211548Notes

Reaction equation

HRID 2211548 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]4[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][C:20]=4[O:28][CH3:29])[CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1.CO.C1COCC1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]4[CH:24]=[CH:23][C:22]([CH:25]([CH3:26])[OH:27])=[CH:21][C:20]=4[O:28][CH3:29])[CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 9867991HCID 9867991, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 21960097HCID 21960097, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a starred solution of 1-[4-[3-[4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]propoxy]3-methoxyphenyl]ethanone (4.1 g, 9.3 mmol) in 60 mi MeOH—THF (1:1) under N2 at ambient temperature, NaBH4 (0.386g, 10.2 mmol) was added portionwise. After complete addition, the reaction was stirred for 3.5 hours and was concentrated to yield a white gum. This was triturated with H2O (2×) and the aqueous fraction was decanted away. Residual water was removed under high vacuum to afford 5.0 of a white powder. The compound was taken up in boiling toluene and the insolubles were filtered away. Concentration of the toluene filtrate afforded 3.8g of a beige solid. Purification via preparative HPLC (Water's Associates prep LC/System 500, using 2 silica gel columns and 2% Et2NH—EtoAc) provided 2.7 g of a light beige solid. The product was recrystallized from EtoAc to afford 1.7g (42%) of a pure white powder, m.p.=113°-115° C.

Workup

  1. additionAfter complete addition
  2. concentrationwas concentrated
  3. customto yield a white gum
  4. customThis was triturated with H2O (2×)
  5. customthe aqueous fraction was decanted away
  6. customResidual water was removed under high vacuum
  7. customto afford 5.0 of a white powder
  8. filtrationthe insolubles were filtered away

Sources & evidence

ORD record
ord-8b180f84d4c74e869e4db0f9576b3903
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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