Methanol → HCID 69600997, compound

HRID 2215085Notes

Reaction equation

HRID 2215085 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@@H:5](/[CH:18]=[CH:19]/[C:20](=[O:28])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4][S:3]1.CO.C([BH3-])#N.[Na+]>C(O)(=O)C>[OH:28][CH:20]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)/[CH:19]=[CH:18]/[C@H:5]1[CH2:4][S:3][C:2](=[O:1])[N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 69601051HCID 69601051, compound

Product 1

HCID 69600997HCID 69600997, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-7 (0.4 g, 1.0 mmol) in 12 mL 5:1 MeOH:acetic acid was added sodium cyanoborohydride (100 mg, 1.4 mmol) and the resulting solution was stirred overnight at room temperature. The solution was quenched with water and was concentrated in vacuo. The concentrate was extracted with ethyl acetate and washed with 2M Na2CO3 and then brine, after which it was dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 60% ethyl acetate/hexanes to yield 400 mg of 3-8 as a colorless oil. Data shown is for the major diastereomer. 1H NMR (400 MHz, CDCl3): δ 7.35–7.21 (m, 5H), 5.84 (dd, 1H), 5.66 (dd, 1H), 4.46 (q, 1H), 4.23 (q, 1H), 4.14 (q, 2H), 3.68–3.37 (m, 2H), 2.97 (dd, 1H), 2.88 (m, 2H), 2.78 (m, 1H), 2.30 (t, 2H), 1.64–1.30 (m, 8H), 1.27 (t, 3H); MS (+ESI): m/z 406.2 (M+1)+.

Workup

  1. customThe solution was quenched with water
  2. concentrationwas concentrated in vacuo
  3. extractionThe concentrate was extracted with ethyl acetate
  4. washwashed with 2M Na2CO3
  5. dry with materialbrine, after which it was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-d7d859de35a14312b039a16b38a3dc96
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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