Tetrahydrofuran → HCID 66747422, compound

HRID 1191963Notes

Reaction equation

HRID 1191963 reaction equation
O[B:2]1[CH2:7][CH:6]=[CH:5][CH:4]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[O:3]1.C[C@@:17]1([OH:27])[C@H:22]([OH:23])[CH2:21][C@@H:20]2[CH2:24][C@H:18]1[C:19]2([CH3:26])[CH3:25].[CH2:28]1COCC1>>[OH:3][CH:4](/[CH:5]=[CH:6]\[CH2:7][B:2]1[O:23][C@:22]2([CH3:28])[C@@H:17]([C@@H:18]3[CH2:24][C@H:20]([CH2:21]2)[C:19]3([CH3:25])[CH3:26])[O:27]1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10219606(+)-PinanediolHCID 66747402HCID 66747402, compound

Product 1

HCID 66747422HCID 66747422, compoundYield 59.9%

Procedure

To a stirred solution of tert-butyl 2-(2-hydroxy-3,6-dihydro-2H-1,2-oxaborinin-6-yl)acetate XLVII (770 mg, 4.58 mmol) in THF (25 mL) was added (1S,2S,3R,55)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol (980 mg, 4.58 mmol) at room temperature. The reaction mixture was stirred for 16 h and concentrated under vacuum. The residue was purified by column chromatography (100% hexane→30% EtOAc/hexane) on silica gel to give tert-butyl (4Z)-3-hydroxy-6-[(1R,2R,6S,8R)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]hex-4-enoate LIV (1 g, 2.75 mmol, 59.9% yield).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by column chromatography (100% hexane→30% EtOAc/hexane) on silica gel

Sources & evidence

ORD record
ord-b88ce3627c8a47aab61f0bcd43c1e207
Source dataset
uspto-grants-2014_03
Patent number
US08680136B2

Reaction notes

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