Acetic Acid → HCID 16755193, compound

HRID 2264148Notes

Reaction equation

HRID 2264148 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][N:13]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:14]([C@@H:16]3[O:21][CH2:20][CH2:19][NH:18][CH2:17]3)=[O:15])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CO.C1COCC1>[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][N:13]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:14]([C@@H:16]3[O:21][CH2:20][CH2:19][N:18]([CH2:30][C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[O:27][CH3:26])[CH2:17]3)=[O:15])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 86582-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 60209722HCID 60209722, compound

Product 1

HCID 16755193HCID 16755193, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.1 g of (−)-(2R)—N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide, 0.05 g of 2-methoxybenzaldehyde, 0.1 g of sodium triacetoxyborohydride, 0.1 mL of acetic acid and 5 mL of THF was stirred overnight room temperature, then concentrated under reduced pressure. The residue was partitioned between 3×10 mL of ethyl acetate and 10 mL of saturated sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. Preparative TLC eluting with 25% ethyl acetate in hexanes gave the product as a resin: [α]D23° C.=5.7° (c=1.0, MeOH); MS (m+1)=469.3; 1H NMR (500 MHz, CDCl3) 7.34-7.21 (m, 2H), 6.93-6.85 (m, 3H), 6.81-6.71 (m, 2H), 4.64 (m, 1H), 4.41-4.17 (m, 6H), 3.3 (m, 1H), 3.81 (d, 3H), 3.73-3.60 (m, 3H), 3.33-3.16 (m, 1H), 3.01-2.88 (m, 2H), 2.71 (m, 1H), 2.53 (t, 1H) 2.39-2.28 (m, 1H), 2.18 (m, 2H), 1.97 (m, 1H), 0.87 (m, 6H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between 3×10 mL of ethyl acetate and 10 mL of saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washPreparative TLC eluting with 25% ethyl acetate in hexanes
  6. customgave the product as a resin

Sources & evidence

ORD record
ord-9dee0a03b8cd46faa6849b283c4843e2
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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