Hydrochloric Acid → HCID 68291918, compound

HRID 712984Notes

Reaction equation

HRID 712984 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:21][C:8]2([CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:7][N:6]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:5]1.[ClH:28]>ClCCl>[ClH:28].[CH3:1][O:2][CH2:3][CH:4]1[CH2:5][N:6]([C:22]2[N:23]=[CH:24][CH:25]=[CH:26][N:27]=2)[CH2:7][C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[O:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70872731Tert-butyl 10-(methoxymethyl)-8-pyrimidin-2-yl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 68291918HCID 68291918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 10-(methoxymethyl)-8-pyrimidin-2-yl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (1.18 g, 3.12 mmol) was dissolved in dichloromethane (2 mL) and treated with a solution of HCl (1.6 mL of 4 M in dioxane, 6.2 mmol). The mixture was allowed to stir for 2 h. The reaction mixture was evaporated to dryness to provide 2-(methoxymethyl)-4-(pyrimidin-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochloride. ESI-MS m/z calc. 278.2. found 279.2 M+1)+; Retention time: 0.68 min (3 min run). 1H NMR (400 MHz, MeOD) δ 8.59 (d, J=5.2 Hz, 2H), 6.99 (t, J=5.2 Hz, 1H), 4.52 (ddd, J=44.3, 13.4, 1.7 Hz, 2H), 4.12-3.97 (m, 1H), 3.56 (ddd, J=26.1, 10.3, 4.9 Hz, 2H), 3.42 (s, 3H), 3.34 (dd, J=10.9, 5.0 Hz, 2H), 3.27-3.19 (m, 2H), 3.13 (dd, J=13.2, 11.1 Hz, 2H), 2.42 (d, J=15.2 Hz, 1H), 1.94 (dd, J=10.7, 4.3 Hz, 2H), 1.74 (ddd, J=15.3, 12.8, 4.4 Hz, 1H).

Workup

  1. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-dde4136e3f844f09946a168e20ed15de
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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