Sodium borohydride → HCID 69640587, compound

HRID 1744215Notes

Reaction equation

HRID 1744215 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][C@H:16]4[C:28]#[N:29])[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[CH2:17][C@H:16]4[C:28]#[N:29])[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66623681HCID 66623681, compound

Product 1

HCID 69640587HCID 69640587, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 558 mg (1.45 mmol) of 45 in THF (6.6 mL) and MeOH (34 mL) was stirred at rt as 400 mg (10.6 mmol) of NaBH4 was added in small portions over 10 min. The reaction was stirred at rt under N2 for 3.5 h, the solvent was evaporated and the residue was dissolved in EtOAc (100 mL) and H2O (50 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2×, 70 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo giving a yellow foam which was used without purification in the next step. Data for 46: TLC, T-2, Rf 0.22; 1H NMR (400 MHz, CDCl3) δ 1.07 (s, 3H, H-18), 3.75 (t, 1H, J=8.7 Hz, H-17α), 5.05 (s, 2H, benzylic-H), 6.75 (d, 1H, J=2.7 Hz, H-4), 6.80 (dd, 1H, J=8.5, 2.7 Hz, H-4), 7.21 (d, 1H, J=8.5 Hz, H-1), 7.33–7.45 (m, 5H, Ar—H).

Workup

  1. additionwas added in small portions over 10 min
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in EtOAc (100 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EtOAc (2×, 70 mL)
  6. dry with materialCombined organic extracts were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customgiving a yellow foam which
  9. customwas used without purification in the next step

Sources & evidence

ORD record
ord-14c21e3b9d734afc9466b7beecfcf146
Source dataset
uspto-grants-2006_03
Patent number
US07015211B2

Reaction notes

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