Hydrochloric Acid → HCID 68727047, compound

HRID 1471387Notes

Reaction equation

HRID 1471387 reaction equation
[BH4-].[Na+].[CH3:3][C@H:4]1[CH2:13][C:12](=[O:14])[CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C@H:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>CO>[OH:14][C@@H:12]1[CH2:11][C:6]2([CH2:7][CH2:8][CH2:9][CH2:10]2)[C@@H:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@@H:4]([CH3:3])[CH2:13]1.[OH:14][C@H:12]1[CH2:11][C:6]2([CH2:7][CH2:8][CH2:9][CH2:10]2)[C@@H:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@@H:4]([CH3:3])[CH2:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 131732745HCID 131732745, compound

Product 2

HCID 68727047HCID 68727047, compoundYield 37%HCID 68771660HCID 68771660, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

At 5° C., NaBH4 (0.26 g, 6.5 mmol) in methanol (25 ml) was treated with a solution of crude cis-ethyl 7-methyl-9-oxospiro[4.5]decane-6-carboxylate (2.2 g, 9.2 mmol) in methanol (10 ml). The resulting mixture was stirred at 20° C. for 4 h, poured into 2N aqueous HCl (30 ml) and ice/water (50 ml), and extracted twice with MTBE (50 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4) and concentrated. FC (180 g SiO2, hexane/MTBE 2:1) of the crude product (2.07 g, cis,cis/cis,trans 39:61) gave rel-(6S,7S,9S)-ethyl 9-hydroxy-7-methylspiro[4.5]decane-6-carboxylate (cis,trans; 0.82 g, 37%) and rel-(6S,7S,9R)-ethyl 9-hydroxy-7-methylspiro[4.5]decane-6-carboxylate (cis,cis; 0.49 g, 22%).

Workup

  1. extractionextracted twice with MTBE (50 ml)
  2. washThe combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cbcd33b570c5467ab666e83ac47953e2
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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