Triethylamine → HCID 10740744, compound

HRID 2396637Notes

Reaction equation

HRID 2396637 reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18][C@@H:19]([C:32]2[CH2:36][CH2:35][CH2:34][CH:33]=2)[O:20]C(=O)NC[C@@]2(C)C=CC=CC2)=[C:16]([O:37][CH3:38])[C:15]([CH3:39])=[C:14]2[C:10]=1[C:11](=[O:40])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[SiH](Cl)Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:1]([O:8][C:9]1[C:17]([CH2:18][C@@H:19]([C:32]2[CH2:36][CH2:35][CH2:34][CH:33]=2)[OH:20])=[C:16]([O:37][CH3:38])[C:15]([CH3:39])=[C:14]2[C:10]=1[C:11](=[O:40])[O:12][CH2:13]2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 131719270HCID 131719270, compound

Product 1

HCID 10740744HCID 10740744, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-{2-[4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl]-1-(S)-[N-(1-(R)-methylbenzyl)carbamoyloxy]eth-1-yl}cyclopent-1-ene (9.0 g) and triethylamine (4.6 ml) in toluene (60 ml) was added trichlorosilane (2.5 ml) dropwise in toluene (20 ml). After addition, the reaction was submerged in an oil bath pre-heated to 110° C. and stirred for 15 minutes, then cooled to room temperature. The reaction was diluted with ethyl acetate (500 ml) and washed sequentially with aqueous ammonium chloride, dilute hydrochloric acid, aqueous sodium bicarbonate, brine, then dried over magnesium sulfate and evaporated onto 90 g of silica gel. This was placed on top of a silica gel column and eluted with 4:1 hexane:ethyl acetate to afford the product 1-[2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-1-(S)-hydroxyeth-1-yl]cyclopent-1-ene, m.p. 112.0°-112.7° C. (ethyl acetate), [α]D =33.11 (CH3OH).

Workup

  1. additionAfter addition
  2. customthe reaction was submerged in an oil bath
  3. temperaturecooled to room temperature
  4. washwashed sequentially with aqueous ammonium chloride, dilute hydrochloric acid, aqueous sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated onto 90 g of silica gel
  7. washeluted with 4:1 hexane

Sources & evidence

ORD record
ord-aad753ac87cb45a2b71487d3f67d4427
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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