Sodium borohydride → HCID 57794759, compound

HRID 2099289Notes

Reaction equation

HRID 2099289 reaction equation
[BH4-].[Na+].[C:3]1([C@@:9]2([CH:21]=[O:22])[CH2:11][C@H:10]2[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[C:3]1([C@@:9]2([CH2:21][OH:22])[CH2:11][C@H:10]2[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57794767HCID 57794767, compound

Product 1

HCID 57794759HCID 57794759, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.2 g, 32.2 mmol, 1 eq) was added in one portion to a mixture of (1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropanecarbaldehyde (7.8 g, 29.3 mmol, 1 eq), accessed via the method of Preparation 19B, in 100 mL ethyl alcohol at ambient temperature. The reaction was stirred at ambient temperature for 18 h, concentrated down and the residue partitioned between ethyl acetate and brine. The organics were dried over Na2SO4, filtered and concentrated to give a yellow oil. The crude material was purified by flash chromatography (SiO2, eluted successively with hexanes and EtOAc/hexanes (1:4)) to give the title product (7.8 g, 29.06 mmol, 99%) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ 7.31-7.15 (m, 10H), 4.61 (t, J=5.7 Hz, 1H), 4.30-4.17 (m, 2H), 3.53-3.48 (m, 1H), 3.35-3.31 (m, 1H), 3.02-2.95 (m, 2H), 1.40-1.33 (m, 1H), 0.96-0.93 (m, 1H), 0.72-0.69 (m, 1H). ES-LCMS m/z 291.2 (M+Na).

Workup

  1. concentrationconcentrated down
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customThe crude material was purified by flash chromatography (SiO2
  8. washeluted successively with hexanes and EtOAc/hexanes (1:4))

Sources & evidence

ORD record
ord-4b421b6ecc044fe281f6e23beda8d23c
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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