2-Amino-2-methyl-1-propanol → HCID 46837651, compound

HRID 1399528Notes

Reaction equation

HRID 1399528 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:13])[C@H:10](O)[CH3:11])[CH:6]=[CH:7][CH:8]=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[NH2:45][C:46]([CH3:50])([CH3:49])[CH2:47][OH:48]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@:9]2([OH:13])[O:48][CH2:47][C:46]([CH3:50])([CH3:49])[NH:45][C@H:10]2[CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 88675Proton spongeHCID 46838207HCID 46838207, compound

Product 1

HCID 46837651HCID 46837651, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 4f was synthesized by a procedure similar to that described for (2S,3S)-4a using (R)-1-(3-methoxyphenyl)-2-hydroxypropan-1-one (10f, 4.2 g, 0.023 mol), Proton sponge (5.9 g, 0.028 mol), triflic anhydride (4.2 mL, 257 mmol), and 2-amino-2-methyl-1-propanol (4.5 g, 0.051 mol) in CH2Cl2 (50 mL). After purification, 4.16 g (71%) of the free base 4f was isolated and converted to 1.24 g the hemi-D-tartrate salt, which had 91% ee: mp 99-100° C.; [α]20D +7.9° (c 1.1, CH3OH); 1H NMR (methanol-d4) δ 7.32 (t, 1H, J=7.8 Hz), 7.19-7.14 (m, 2H), 6.96-6.92 (m, 1H), 4.33 (s, 1H), 4.18 (d, 1H, J=12.3 Hz), 3.81 (s, 3H), 3.52 (d, 1H, J=12.3 Hz), 3.48-3.45 (m, 1H), 1.59 (s, 3H), 1.34 (s, 3H), 1.06 (d, 3H, J=6.6 Hz). 13C NMR (methanol-d4) δ 178.8, 161.4, 144.1, 130.7, 120.1, 115.4, 113.8, 97.1, 75.2, 67.6, 56.1, 55.2, 24.4, 21.5, 14.5; LCMS (ESI) m/z 252.3 [(M-tartrate)+, % M=C16H24NO6]; Anal. (C16H24NO6.0.5H2O) calcd: C, 57.30; H, 7.51; N, 4.18. found: C, 57.33; H, 7.55; N, 4.14.

Workup

  1. customCompound 4f was synthesized by a procedure similar to
  2. customAfter purification

Sources & evidence

ORD record
ord-6c6fc4facc4f4f37a21c4d9d0e8c21a2
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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