2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 131736562, compound

HRID 1479105Notes

Reaction equation

HRID 1479105 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH2:24][CH2:25][NH:26][CH3:27])=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:28].[C:29]([Si:33]([CH3:39])([CH3:38])[O:34][CH2:35][CH:36]=O)([CH3:32])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:29]([Si:33]([CH3:38])([CH3:39])[O:34][CH2:35][CH2:36][N:26]([CH3:27])[CH2:25][CH2:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]([N:13]1[CH2:12][C:7]2=[C:8]3[N:4]([N:5]=[C:6]2[CH2:14]1)[C:3]([CH3:28])=[C:2]([Cl:1])[C:10]([CH3:11])=[N:9]3)=[O:16])([CH3:30])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 122436378HCID 122436378, compound

Product 1

HCID 131736562HCID 131736562, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of Example 144 (100 mg; 0.25 mmol; 1 eq.), (tert-butyl-dimethyl-silanyloxy)-acetaldehyde (87 mg; 0.50 mmol; 2 eq.) and sodium triacetoxyborohydride (58 mg; 0.28 mmol; 1.1 eq.) in DCE (10 mL) was stirred at 70° C. for 1 hour. The solution was washed with 0.1M NaOH (2×), dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography (EA to 10% MeOH in EA) afforded the title compound (45 mg, 32%) as a yellow oil. HPLC (max plot) 95.0%, Rt 4.26 min. UPLC/MS: (MS+) 558.3 ([M+H]+).

Workup

  1. washThe solution was washed with 0.1M NaOH (2×)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (EA to 10% MeOH in EA)

Sources & evidence

ORD record
ord-acb9d0a4ef304d0fa7a5baa21de103d5
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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