Sodium borohydride → HCID 67591872, compound

HRID 346017Notes

Reaction equation

HRID 346017 reaction equation
[C:1]1([S:7][CH:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)[CH:15]=3)[O:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.O1CCCC1>[C:1]1([S:7][C@H:8]2[C@H:17]([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)[CH:15]=3)[O:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19600853HCID 19600853, compound

Product 1

HCID 67591872HCID 67591872, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the title product of Example 63 (1.85 g, 0.00447 mol) in 70 ml of methanol at 0°-5° C. was added in portions 208 mg (0.00538 mol) of sodium borohydride. The reaction was warmed with stirring to room temperature, then diluted with 20 ml of tetrahydrofuran to obtain a homogeneous mixture, which, after stirring for 1.2 hours was concentrated in vacuo and the residue taken up in 400 ml ethyl acetate, washed with H2O and brine, dried over Na2SO4, and concentrated carried out by silica gel column chromatography eluting with 20% ethyl acetate/CH2Cl2. The less polar cis-title product was isolated as a white solid (1.11 g, 60%). Recrystallization from isopropanol/hexanes gave 1.04 g of white crystals, m.p. 144°-146° C. The more polar trans-title product was obtained as a mixture, contaminated with a small amount of the less polar product. It was re-chromatographed using the same eluant to yield 400 mg (22%) of trans-title product as a white foamy solid. Recrystallization from toluene-hexanes afforded 280 mg of white crystals, m.p. 100°-102° C.

Workup

  1. temperatureThe reaction was warmed
  2. customto obtain a homogeneous mixture, which
  3. stirringafter stirring for 1.2 hours
  4. concentrationwas concentrated in vacuo
  5. washwashed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. washeluting with 20% ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-806c2d1c2a0d4975b57227de36bd8dc5
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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