Diethyl Ether → HCID 86751136, compound

HRID 726815Notes

Reaction equation

HRID 726815 reaction equation
[BH4-].[Li+].CO[C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:14][C:13]2[CH:15]=[C:16]([CH:19]([OH:27])[CH2:20][CH2:21][C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:17]=[CH:18][C:12]=2[O:11]1.CC[O:31]CC>>[OH:27][CH:19]([C:16]1[CH:17]=[CH:18][C:12]2[O:11][CH:10]([CH:9]([OH:31])[CH2:8][CH2:7][CH2:6][CH3:5])[O:14][C:13]=2[CH:15]=1)[CH2:20][CH2:21][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 18972191HCID 18972191, compound

Product 1

HCID 86751136HCID 86751136, compoundYield 98%

Procedure

Lithium borohydride (2.1 mg, 0.096 mmol) was added to a solution of (±)-methyl-5-[[6-(1-hydroxy-3-(2-thienyl)propyl]-1,3-benzodioxolyl]pentanoate (Compound 73, 36.0 mg, 0.096 mmol) in Et2O (2.0 mL) at 23° C. After 12 hours the reaction was quenched with 1N NaOH, stirred 1 hour, and extracted with EtOAc. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash column chromatography (silica gel, 2:1 hex/EtOAc) provided 32.6 mg (98%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 7.14 (d, J=5.5 Hz, 1H), 7.01 (s, 1H), 6.93 (dd, J=3.3, 5.5 Hz, 1H), 6.84 (d, J=3.3 Hz, 1H), 6.61 (s, 1H), 5.92 (s, 2H), 4.88-4.92 (m, 1H), 3.63 (t, J=5.7 Hz, 2H), 2.97-3.03 (m, 2H), 2.43-2.49 (m, 2H), 1.84-2.20 (m, 3H), 1.26-1.59 (m, 7H).

Workup

  1. customAfter 12 hours the reaction was quenched with 1N NaOH
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel, 2:1 hex/EtOAc)

Sources & evidence

ORD record
ord-c3a9bd67f74246b4811ec809ce656857
Source dataset
uspto-grants-1998_01
Patent number
US05710288

Reaction notes

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