Methylamine → HCID 86587926, compound

HRID 459070Notes

Reaction equation

HRID 459070 reaction equation
C1COCC1.[CH3:6][NH2:7].[CH3:8][C:9]([Si:12]([CH3:47])([CH3:46])[O:13][C@H:14]([C@@H:19]([CH3:45])/[CH:20]=[C:21](/[CH3:44])\[CH2:22][C@H:23]([CH3:43])[C@@H:24]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C@H:25]([CH3:34])[C@@H:26]([OH:33])[C@@H:27]([CH3:32])/[CH:28]=[CH:29]\[CH:30]=[CH2:31])[C@@H:15]([CH3:18])[CH:16]=O)([CH3:11])[CH3:10]>CC(O)=O.CCOC(C)=O>[CH3:40][C:39]([Si:36]([CH3:38])([CH3:37])[O:35][C@H:24]([C@@H:23]([CH3:43])[CH2:22]/[C:21](/[CH3:44])=[CH:20]\[C@H:19]([CH3:45])[C@@H:14]([O:13][Si:12]([C:9]([CH3:8])([CH3:11])[CH3:10])([CH3:47])[CH3:46])[C@@H:15]([CH3:18])[CH2:16][NH:7][CH3:6])[C@H:25]([CH3:34])[C@@H:26]([OH:33])[C@@H:27]([CH3:32])/[CH:28]=[CH:29]\[CH:30]=[CH2:31])([CH3:41])[CH3:42]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 86760454HCID 86760454, compound

Product 1

HCID 86587926HCID 86587926, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred THF solution of methylamine (2 M, 1.01 mL, 4 eq, 2.02 mmol) is added THF (10 mL) solution of (2R,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-3,9-bis[[(1,1-dimethylethyl) dimethylsilyl]oxy]-11-hydroxy-2,4,6,8,10,12-hexamethyl-5,13,15-hexadecatrienal (300 mg, 0.505 mmol, 1 eq) at 23° C. After stirring for 20 minutes, NaBHAc3 is added followed by addition of 1 drop of AcOH. The solution is stirred for an additional 2 hours and diluted with EtOAc (10 mL), washed with aqueous saturated Na2CO3 (2×5 mL), brine, dried with Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography (silica gel, gradient 10–30% MeOH/EtOAc) to give the desired compound (180 mg, 59%) as a colorless oil.

Workup

  1. additionNaBHAc3 is added
  2. stirringThe solution is stirred for an additional 2 hours
  3. washwashed with aqueous saturated Na2CO3 (2×5 mL), brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (silica gel, gradient 10–30% MeOH/EtOAc)

Sources & evidence

ORD record
ord-2ef8b642882f407e92a1743df3ab9e4f
Source dataset
uspto-grants-2007_03
Patent number
US07192980B2

Reaction notes

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