Sodium borohydride → HCID 11340988, compound

HRID 1064756Notes

Reaction equation

HRID 1064756 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1.[BH4-].[Na+]>C(O)C.O1CCCC1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([CH:24]([OH:26])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 9884652HCID 9884652, compound

Product 1

HCID 11340988HCID 11340988, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 136C (46 mg, 0.12 mmol) in ethanol (2 mL) and tetrahydrofuran (0.5 mL) was treated with sodium borohydride. The mixture was concentrated and passed through a short column of silica with a gradient of 2 to 10% MeOH/CH2Cl2. The resulting residue rinsed with ether, dissolved into methanol (1 mL), treated with 0.1 M aqueous hydrochloric acid (0.2 mL) heated at 60□ C for three hours, treated with more 0.1 M aqueous hydrochloric acid (0.05 mL), heated at 60□ C for one hour, concentrated, and chromatographed through a short column of silica with a gradient of 2 to 10% 2 M NH3 in MeOH/CH2Cl2 to provide the title compound as a white powder (11% yield). 1HNMR (300 MHz, CD3OD) δ 1.17 (d, 3 H), 1.4-1.54 (m, 1 H), 1.49 (d, 3 H), 1.73-1.86 (m, 2 H), 1.95-2.08 (m, 1 H), 2.24-2.36 (m, 1 H), 2.43-2.60 (m, 2 H), 2.93-3.14 (m, 2 H), 3.19-3.33 (m, 2H), 4.89 (q, 1 H), 6.59 (s, 1 H), 7.32 (ddd, 1 H), 7.39 (dd, 1 H), 7.45-7.47 (m, 2 H), 7.49 (ddd, 1 H), 7.62 (m, 1 H), 7.71 (dd, 1 H).

Workup

  1. concentrationThe mixture was concentrated
  2. washThe resulting residue rinsed with ether
  3. dissolutiondissolved into methanol (1 mL)
  4. additiontreated with 0.1 M aqueous hydrochloric acid (0.2 mL)
  5. temperatureheated at 60□ C for three hours
  6. additiontreated with more 0.1 M aqueous hydrochloric acid (0.05 mL)
  7. temperatureheated at 60□ C for one hour
  8. concentrationconcentrated
  9. customchromatographed through a short column of silica with a gradient of 2 to 10% 2 M NH3 in MeOH/CH2Cl2

Sources & evidence

ORD record
ord-98127d322f0640f08fae572577f2ef1c
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Reaction notes

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