Diethyl Ether → HCID 86751136, compound

HRID 2256272Notes

Reaction equation

HRID 2256272 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 F, 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) δ7.14 (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-4c07148fa98048128bffc4ba9cd07647
Source dataset
uspto-grants-1997_08
Patent number
US05654329

Reaction notes

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